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Synthesis of a tetracyclic, conformationally constrained analogue of delta8-THC.

Abstract：

:A tetracyclic, conformationally constrained analogue of delta8-THC (2) has been synthesized in which a two carbon bridge exists between C2 and C2'. Two conceptually related syntheses of 2 are described, both of which employ 5,7-dimethoxy-4-oxo-1,2,3,4-tetrahydronaphthoic acid (11) as starting material. This substrate was converted to 5,7dimethoxy-2-propyl-1,2,3,4-tetrahydronaphthalene (7) and its 4-keto derivative (18). Demethylation of 11 and 18 provided the corresponding resorcinols, which were condensed with trans-p-menthadienol to afford cannabinoid 2, and a keto derivative (20). LiA1H4/A1C1(3) reduction of 20 provided 2. Cannabinoid 2 has relatively low affinity for the cannabinoid brain receptor (Ki = 703+/-98 nM).

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Huffman JW,Yu S

doi

10.1016/s0968-0896(98)80008-4

subject

Has Abstract

pub_date

1998-12-01 00:00:00

pages

2281-8

issue

12

eissn

0968-0896

issn

1464-3391

pii

S0968089698800084

journal_volume

6

pub_type

杂志文章

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